There was a stretch early in my one-person path when everything stalled.
One of my main clients paused their launch. They said they wanted everything to be perfect before going live and I get it. But perfection meant delay. And delay, for me, meant two-thirds of my income vanished overnight.
I cut my gigs down to a third of what I’d planned. My calendar went quiet. I spiraled a little. I started doing the math, wondering how long I could float, debating whether this path made sense at all. I remember waking up one morning and thinking: This again? Am I really still doing this?
That’s when I wrote this.
Not as a roadmap or a pep talk but as a way to remember what was real when everything felt like it was falling apart.
Some mornings I wake up and wonder what I was thinking.
I left a good job. A well-paying one, at that. The kind of job people around me admired—stable, respectable, an achievement in its own right. I didn’t leave because it was terrible. I left because I couldn’t shake the feeling that something was off. That even though everything looked right, it didn’t feel right.
I thought I’d be brave. I thought I’d start from scratch and build something of my own. What I didn’t anticipate was how often I’d want to quit.
Not just in the abstract sense. I mean quit in the real way: polishing up my resume, scrolling through job listings, imagining the neatness of a fixed salary and a predictable schedule. There have been weeks when I woke when while the world was still dark, hours before anyone stirred—when even the sun seemed to be sleeping in, then worked all day, and still felt like I was moving nowhere. Weeks when I sent a hundred cold emails and got either silence or curt replies that said, in effect, Don’t bother us again.
I resented it. I resented myself. I resented the strangers who ignored my efforts. I resented the well-dressed workers on the train with clear destinations and clear paychecks. I resented the structure of a world I voluntarily stepped away from.
And most of all, I forgot why I started.
It’s strange how easily we lose sight of our original dreams once reality sets in. Those early days held such clarity, the late-night inspiration, the quiet thrill of imagining a life built around your creativity, the longing to create something genuinely yours. But the day-to-day struggles blur these memories. Little by little, without noticing, the reasons slip away until you're left only with the grind and the doubt.
Every creator knows this quiet forgetfulness, the slow fade of your initial excitement as reality wears it thin. It’s not sudden or dramatic, just subtle erosion over countless unanswered emails and silent mornings, until one day you wake up wondering why you even began.
The Reason Disappears
One of the hardest things about doing something hard is that the reason you’re doing it disappears just when you need it most. It’s easy to be inspired before anything goes wrong. It’s easy to be romantic when you’re still on the runway, making plans. But once you're midair, when you’ve used up your fuel and the clouds don’t part, inspiration isn’t loud anymore. It’s barely a whisper.
At some point, you forget. You forget the late-night excitement, the idea that wouldn’t leave you alone, the pull toward autonomy or meaning or art or ownership or truth. You forget the frustration you felt in meetings that never went anywhere, the sense that you had to ask permission to be yourself. You forget the decision wasn’t made in haste. It came slowly, painfully, with great deliberation. But memory is selective. Pain isn’t.
The thing is, I don’t think I’m alone in this. I think most people who do work those matters, work that breaks the mold, that’s self-directed, that doesn’t follow a script, go through this. Some quietly return to a more conventional life. Some stick it out, but numb themselves to the hardship. The few who continue and stay awake in the process are the ones I most admire.
But even they, I suspect, have had days like mine.
The Real Difficulty
People think the hard part is finding clients. Or getting traction. Or making money. And yes, those things are hard. But they’re not the hardest.
The hardest part is showing up again the next day when nothing worked the day before. It’s the emotional energy of continuing. Of believing in something invisible. Of seeing zero progress for weeks or worse, backward movement and still choosing not to revert to safety.
Most systems in life are designed for consistency, not volatility. Traditional paths reward steadiness, de-risked decisions, and socially legible milestones. If you’re doing something off that path, you have to build your own stability. You can’t borrow credibility from a company name. You can’t outsource direction to a manager. You are the institution now.
Which means the emotional swings are sharper. There’s no insulation. You deal with your self-doubt raw, in the open, while trying to work through it.
That’s what makes it brutal.
And yet, amid this brutality, there remain moments—small, gentle reminders—that reconnect you, ever so briefly, to why you chose this path in the first place.
Some days, your presence is the only reason I keep writing.
If this met you in a low moment and you’d like to give something back, you can support me and get a Notion template I made for tracking your daily rhythm and energy on Buy Me a Coffee.
Excellent article. Brilliantly written. ✌️✌️
Lose it to regain it, forget it to remember it, in and out and around and around...thanks for structing this how you have.
Rosalie - you share the sense of self awareness and doubt we all experience when we risk it all and go out on our own! It’s a lot of persistence and showing up for ourselves and those who we will serve in the future that we can’t see yet. Maybe they are what’s pulling you to not give up— and to reach them somehow and tell them about the journey. Cause they need to know.